Default HTG hotel image

Middletown Springs Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Middletown Springs holiday rentals

Spa

Comfy Cottage with Private Hot Tub in Historic East Poultney

Comfy Cottage with Private Hot Tub in Historic East Poultney
Poultney
10.0 out of 10, Exceptional, (13 reviews)
"Very comfortable and clean cottage in a beautiful village. The shower in the bath is incredible. "
United States
Karen C.
The price is HK$1,685
HK$3,046 total
includes taxes & fees
26 Jul - 27 Jul
Comfy Cottage with Private Hot Tub in Historic East Poultney
TV, DVD player

Quaint, friendly cottage with lakefront location & water views

Quaint, friendly cottage with lakefront location & water views
Poultney
9.4 out of 10, Exceptional, (59 reviews)
"The cottage is in a nice spot on the lake. It is accurately depicted in the listing and was great for our trip"
United States
Jim V.
The price is HK$823
HK$3,382 total
includes taxes & fees
23 Jul - 24 Jul
Quaint, friendly cottage with lakefront location & water views
Exterior

Unique family-friendly Vermont cabin!

Unique family-friendly Vermont cabin!
Fair Haven
10.0 out of 10, Exceptional, (19 reviews)
"Awesome places today stay "
United States
James L.
The price is HK$1,404
HK$2,321 total
includes taxes & fees
20 Jul - 21 Jul
Unique family-friendly Vermont cabin!
Exterior

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
Fair Haven
9.0 out of 10, Wonderful, (31 reviews)
"The house was great. We loved the antiqueness of the house. We are technicologically challenged, so had trouble with the TV. The beds were comfortable. We didn't use it, but the kitchen was great. We would definitely use this house again."
United States
Stephanie
The price is HK$1,404
HK$2,501 total
includes taxes & fees
20 Jul - 21 Jul
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
Property grounds

Beautiful 1-bedroom cabin with AC in wonderful Wells

Beautiful 1-bedroom cabin with AC in wonderful Wells
Wells
The price is HK$882
HK$1,163 total
includes taxes & fees
29 Jul - 30 Jul
Beautiful 1-bedroom cabin with AC in wonderful Wells
Microwave, oven, stovetop, dishwasher

Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is HK$2,939
HK$5,767 total
includes taxes & fees
17 Jul - 18 Jul
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Living area

The Family Retreat At Bomoseen 4 Bedroom Home

The Family Retreat At Bomoseen 4 Bedroom Home
3.0 star property
Castleton
The price is HK$2,602
HK$7,210 total
includes taxes & fees
22 Jul - 23 Jul
The Family Retreat At Bomoseen 4 Bedroom Home
Fridge, microwave, oven, stovetop

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"Great stay as always. "
United States
debbie r.
The price is HK$670
HK$1,365 total
includes taxes & fees
19 Jul - 20 Jul
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (28 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
The price is HK$612
HK$1,824 total
includes taxes & fees
22 Jul - 23 Jul
Mountain Green
TV

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
The price is HK$1,440
HK$5,421 total
includes taxes & fees
17 Jul - 18 Jul
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Smart TV, books

Cozy Moonship Yurt in the woods

Cozy Moonship Yurt in the woods
West Rutland
10.0 out of 10, Exceptional, (1 review)
"Clean and cozy with a working hot tub. Would highly recommend"
United States
Justin E.
The price is HK$1,568
HK$3,011 total
includes taxes & fees
28 Jul - 29 Jul
Cozy Moonship Yurt in the woods
Dining

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (12 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is HK$713
HK$1,628 total
includes taxes & fees
12 Aug - 13 Aug
Cozy Rutland Retreat
Coffee/tea maker, fridge, microwave, oven

Centrally located apartment for the skier & outdoor enthusiast

Centrally located apartment for the skier & outdoor enthusiast
Rutland
The price is HK$1,029
HK$2,584 total
includes taxes & fees
17 Jul - 18 Jul
Centrally located apartment for the skier & outdoor enthusiast
Indoor pool

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Okemo Village
10.0 out of 10, Exceptional, (64 reviews)
"The host is extremely friendly and accommodating! The place is large and didn’t feel cramped with two adults and five male teenagers! Perfect in every way, clean, well stocked, and easy access to the slopes!"
United States
Nina
The price is HK$3,527
HK$6,581 total
includes taxes & fees
17 Jul - 18 Jul
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Smart TV, fireplace, video games, books

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is HK$1,129
HK$3,951 total
includes taxes & fees
19 Jul - 20 Jul
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Interior

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"No interaction with host but all amenities were excellent "
United States
Dan M.
The price is HK$1,234
HK$3,195 total
includes taxes & fees
17 Jul - 18 Jul
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Children’s area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (14 reviews)
"Nice place "
United States
Janja L.
The price is HK$710
HK$2,548 total
includes taxes & fees
19 Jul - 20 Jul
Cozy Bromley Retreat
Interior

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Rutland
10.0 out of 10, Exceptional, (5 reviews)
"House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. "
United States
Dominic C.
The price is HK$1,693
HK$3,669 total
includes taxes & fees
21 Jul - 22 Jul
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Private kitchen

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is HK$698
HK$1,800 total
includes taxes & fees
28 Jul - 29 Jul
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Private kitchen

Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home
3.0 star property
North Sherburne
The price is HK$2,687
HK$5,901 total
includes taxes & fees
31 Jul - 1 Aug
Killington A-frame 2 Bedroom Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Springs Hotel Reviews

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

10/10 Excellent
"Staff was very nice and went extra miles with finding activities I was interested in doing."
Alex 5-night trip
Posted less than an hour ago
Best Western Inn & Suites Rutland-Killington

Find out more about Middletown Springs

Search for holiday rentals in Middletown Springs on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown Springs using one of the methods below:

  • View our selection of featured holiday rentals in Middletown Springs
  • Use the map to find apartments and other holiday homes in the Middletown Springs neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown Springs while they last

Look no further and take a look at our great range of rental properties in Middletown Springs!

Frequently asked questions

Can I find holiday rentals in Middletown Springs?

Yes, there are holiday rentals close to the most popular sights in Middletown Springs, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middletown Springs has to offer?

Private Adirondack Getaway. Close to hiking trails, fishing, public beach.: This holiday home rental outside of Middletown Springs is located next to a golf course, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Middletown Springs?

While exploring the area, visit family-friendly sights like Pond Hill Ranch and Pro Rodeo, or get outside and enjoy nature at Mineral Springs Park. In the wider area, you’ll find Middletown Springs Public Library and Lake Saint Catherine State Park.

What are holiday rentals like in Middletown Springs?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown Springs. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips.